With You
by VeraAGM
Summary: In a heartbreaking second, Blair Waldorf realized that Chuck Bass may still see her as the girl who made mud pies with him when she was five and cried whenever he snapped her headbands. But she was going to change his mind, desperation be damned. B x C N x S
1. Prologue

**AN: This is my second time writing a fanfiction. Please be gentle, and let me know what you think. This will be a short story (ten chapters at most). It is sort of AU and will be Blair and Chuck centric (with hints of Serena, Nate and Dan along the way).**

 **All the characters are still in the Upper East Side with a few tweaks in their relationships with each other.**

* * *

 **WITH YOU**

by: VeraAGM

 _I don't want this moment to ever end_  
 _Where everything's nothing without you_  
 _I'll wait here forever just to, to see you smile_  
 _'Cause it's true: I am nothing without you_

 _-With Me by Sum 41, played during 1 x 07 (Victor Victrola)_

* * *

Prologue

Blair Waldorf had always considered herself an extraordinarily lucky girl. Admittedly, she was born with a gold spoon in her mouth and grew up in a reasonably loving household with two indulging parents and a doting and devoted Dorota. During restless nights, when she would contemplate over how the Humphreys managed to survive in the cabbage patch they called home or how the students who enrolled into Constance and St. Judes with a scholarship coordinated their meager lifestyle, she would snuggle in her bed and hug her bolster a little tighter.

Despite spotting her father naked and in love with someone who was not her mother or watching her best friend jaywalk through the streets of Manhattan with alcohol stained breath, Blair had complete and utter conviction in her chance. It had not failed her during the divorce, when she finally parted from Nathaniel Archibald or after those horrible pregnancy rumors were spread. Ultimately, she had a proper home to go to, a California king bed to sleep in and enough money to fill her penthouse twice.

Therefore, when she saw _him_ during the graduation soiree, she could hardly believe that her luck could _deceive_ her. For the first time in eighteen years, she was utterly and completely confused.

Even to her, the soiree was not an affair to be taken gingerly. It did not make New York Times headlines nor did it receive accolades from Vogue; it was an opulent yet intimate gathering. Cold curtains were drawn back to reveal golden hues, gold tiaras were traded in for diamond crowns, and lacrosse uniforms were substituted with Dior suits. The Upper East Side took a hiatus from its scheming to display a perfect facade constructed of faux tears and nervous laughter. Every freshly graduated student was paired up with alumni from the school they were attending, and together, each duo was to spend a night mingling and lavishing themselves with drinks. After all, it was not every day that Constance lets its genteel, aristocratic and dignified birds fly to the real world and not allow it to come back.

Lily van der Bass, who had taken over the duties of organizing the event, had conditioned Constance's own yard until it boasted affluence. The theme was midnight-the start of a new day, a fresh era for the future heirs. Strings of light had been artistically placed upon the hall while purples, navy, and hints of green peeked out from the radiance.

Blair, as per usual, had taken her time to perfect and mold herself until she was the epitome of midnight darkness. Her Valentino dress was a deep navy mixture of chiffon and tulle, sprinkled with gold specks that clustered around her waist and orbited throughout the bodice. Manolo Blahniks added length to her petite frame while expertly loosened curls framed her face. With painted lips and darkened lids, she walked briskly down the corridors of her school with a Waldorf original hanging off of one hand and a slightly tipsy best friend on the other.

Serena opted for a shimmery silver dress that hung off her shoulders and stopped near at her ankles. Golden ringlets, glossy lips and metallic shoes added to the siren who was the darling of the van der Basses. Blair's stomach had clenched when she first saw her. Her days of purging were long over, but she could not help but blink twice at the blonde's perfectly shaped legs that peeked out from the shiny fabric or the way her hips swayed perfectly as she walked.

Serena was fortunate in every way, Blair had concluded as she watched the her untangle her fingers to join the cabbage patch, his parents, and her family. Maybe, Serena was even luckier than her. Bart had managed to take a pause from his engrossing schedule to attend his little girl's graduation while Lily had been there for her daughter every step of the way. Eleanor, on the other hand, had hopped on a jet to Italy to showcase her collections on yet another runway while her father had sent a "congratulations" card from Paris with a picture of him and Roman in the front.

 _You should consider yourself lucky that your admissions officer was a client of mine,_ her mother had chastised after she reminded her about the event _. With the drama you pulled with the Archibalds this year and the many classes you missed during sophomore year due to your...condition, it's a miracle that you got into Yale. At the rate you were going in, I was sure I would have to make some appropriate donations to even get you accepted to Cornell or NYU._

Sucking in a breath, Blair plastered a smile as the lights illuminated her. Her mother was right; she always was. She was the most fortunate girl in the world. Her wealth and chance had landed her a spot to the prestigious university. Her golden spoon had saved her yet again.

 _No need to mope,_ she reminded herself. _You're finally where you wanted to be._

And she was. She had waited with a baited breath for the graduation soiree to come because it would put an end to the rule of Gossip Girl and perhaps change her from THE Blair Waldorf, the perfect queen of the Upper East Side, to simply Blair Waldorf, an eighteen year old girl with flaws and failures. The suffocation would end.

Sighing, she separated from her posse to stand near a quiet corner and tapped her foot as she waited for her partner to show up. Serena, much to both their disappointment and Dan's dismay, had been paired up with Carter Baizen while Nate had matched with Bree Buckley. Kati had Chairlay Bloomberg while Iz had Anastasia Hilton. Nearly everyone had known or heard of their mentor except her. All she was aware of was that his or her first name started with a C. Apparently, he or she had requested to keep the identity anonymous till the party itself started.

Sighing for the umpteenth time, she closed her eyes and let the music wash over her. It was loud and made her skin tingle and lungs feel like mush. The bass thumped in time with her heartbeat as they were one, filling her from head to toe. As much as she hated to admit it, Rufus Humphrey was an astonishingly brilliant musician. Over the roar of music, a distant, hazy chatter could be heard. She couldn't make out any words, but laughter rang in her ears and wouldn't seem to stop. So what if her mentor didn't show up? She had waited for to long to turn this event into just another night. The song that was playing got louder, pulling her in and not letting her go. She had no choice but to join, sway her hips slightly and move her head with the tune.

 _"A girl like you shouldn't be dancing alone."_

She had almost missed the voice. The acoustics were intense and thundering, but it was the way her back was pricking, and the little hairs on her neck stood up that she realized someone was speaking to her. The only time that had ever happened was...no. Her eyes dilated, throat dried and Blair was sure she was going to lose consciousness.

 _"Waldorf, I know you recognize me."_

She turned slightly, ignoring the thudding of her heart and the lump in her throat. There stood Chuck Bass, in a spotless Brioni Vanquis suit and looking as handsome as the devil. His hair was gelled but tousled every so gently that it lent an air of boyishness to his appearance. His eyes were sharper, nose slightly crooked and lips poised into his signature smirk.

 _"I...Charles,"_ she managed to croak out.

He let out a throaty chuckle that made her heart skip slightly. " _So you do remember me, but I still go by Chuck. How's my sister's best friend doing these days?"_

And then suddenly, the trance that had bound her snapped. It had been years since she last saw him, but here he was, still imagining her as his sister's friend. In a heartbreaking second, Blair Waldorf realized that Chuck Bass will forever see her as the girl who made mud pies with him when she was five and cried whenever her headbands broke.

 _"I'm doing well,"_ she responded coolly, swallowing the lump of dejection that formed in then back of her throat. _"How are you?"_

 _"Peachy,"_ he waved his hand in the air at a random bystander as if he were a celebrity. _"What are you doing here in the corner? Where are Mati, Peppy and Iz."_

 _"Kati and Penelope,"_ she corrected. _"Are talking to their partners and I'm waiting for mine to show up."_ She spared a glance at her phone before looking up. _"He's late by 20 minutes."_

Chuck leaned back curiously and watched her with hooded eyes. _"You know for someone who is going to a school like Yale, you're being horribly obtuse."_

Blair furrowed her eyebrows, her stomach sinking at the playful jeer. _"Go away Chuck and let me wait for in peace."_

He shot her a knowing look.

 _"You're C,"_ she articulated.

 _"Bingo."_

 _"I'm sorry,"_ she apologized, dusting off the imaginary specks from her gown. _"It's been a long day, and I need a drink. I thought you already graduated. "_

 _"I was supposed to,"_ he disclosed. _"But I took a semester off, but don't worry, you'll be seeing me around Yale. I'm still going there for graduate school."_

 _"That's great,"_ she said candidly. _"It will be nice to see a-" hot, wonderfully sexy, astonishingly handsome "-familiar face every day."_

 _"Hmm,"_ Chuck replied, his voice husky. " _We can finally spend some quality time together...without my sister."_

Ignoring those damn butterflies that now flew violently in her stomach and the heat the pooled between her legs, she twisted her head until she was no longer looking at his eyes. _"So why the secrecy?"_

 _"How about I grab you a drink?"_

He had almost disappeared when he twisted his face into a sly smile and bent down close to her ear. _"And oh, I forgot to tell you. You look beautiful, a thousand times better than Rose."_

And thus, with a sinking heart and flushed cheeks, Blaire Waldorf realized that Chuck Bass had not forgotten her confession even after so many years.

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 **Reviews are greatly appreciated! Let me know if I should continue this or not. Future chapters will definitely be longer than this.**


	2. Chapter 1: Heartbreak

Chapter 1: Heart Break

* * *

Isn't it lovely, all alone?  
Heart made of glass, my mind of stone  
Tear me to pieces, skin and bone  
Hello, welcome home

-Lovely by Bille Eilish

* * *

 _6 years ago (Age 11-12)_

 _Two days before her eleventh birthday, Blair's mother called her fat. The insult had been hurled at her in a moment of anger because she refused to wear what her mother had picked out for her party and she had told, rather bluntly, that she preferred what Dorota had chosen. Her mother's choice of attire had been a bottle green that reminded her of a turtle while Dorota had picked out a soft pink that complemented her skin tone. Eleanor's cheeks reddened with fury, and she quickly grabbed her daughter's face and whispered with cruel words to her._

 _"My design would look lovely on you, dear," she had jeered, harshly tugging at the hem of Blair's dress which refused to slide over her chest. "If you weren't so fat."_

 _She had heard hints about her weight before, snide little remarks regarding how she shouldn't wear a particular outfit because it accentuated her tummy or how she should suck in her breath so the weight transfers to her chest and not her stomach. But never fat; it was foreign to her ears. Her mother had attempted to apologize, and Blair could see that there was some sincerity in her eyes, but it was too late. The word swirled around her like a puff of smoke. It blanketed and choked her until she felt as if her lungs had turned into dark sponges and her heart had concrete poured all over it._

 _Sitting down in front of her bedroom mirror, she stripped herself down to her training bra and skirt before probing at the little flab that protruded out every time she leaned forward. As her mind span in its usual carousel of thoughts, she deduced that her mother was right. It would take days, even years, for her to get rid of the extra skin hanging awkwardly on her body, but she would try. Oh yes, she would work until all this...this ugliness evaporated._

 _She bit her lips and stared at the knife in front of her. She could slice it off, carve off the chunks until she had a Serena-like, Victoria's secret model-esque body underneath. Holding the knife tightly, she gently connected the tip to her flesh until a thin, thread-like maroon line surfaced._

 _"Even your ideas are horrible," she whispered after a second, throwing the knife as far away from her as possible. Putting her shirt back on, Blair pulled her brown hair into a tight pony-tail and applied gloss on her cheeks and mascara on her eyelash. A pretty girl stared back after she was done; a girl with the intelligence, beauty and shrewdness to be a queen, a ruler, but all she saw was someone ordinary, incapable and worthless. Someone who did not deserve to be a Waldorf._

 _She jabbed harshly at her hips until the spot was numb with pain and crescent-like impressions on her skin and her white shirt had tiny droplets of scarlet scattered through it._

 _"What the hell are you doing?"_

 _Straightening her back, Blair gave a horrified glance to the lanky boy outside her room."Don't you know how to knock?"_

 _Ignoring her, Chuck Bass, with his stupid pink scarf and equally horrendous bow tie, made his way to her bed and propped himself down as if it was his own._

 _"Get out Chuck," her voice threatened as she concealed the spots on her shirt with her arm._

 _"Were you trying to cut yourself?" He said after a while, eying the sharp scissors, the stained knife that littered her carpeted floor and the blood on her shirt._

 _"Of course not. I just wanted to-" slice off fat "-take off the price tag from my new Dolce and Gabbana skirt. I accidentally cut myself in the process."_

 _He eyed her skeptically. "You cut your stomach and hips instead of your fingers?"_

 _"Why are you here Chuck?" She asked quickly, folding her hands over so an air of superiority appeared over her. "And yes, I did. Why do you care?"_

 _"I don't." Snuggling himself into the bed, he threw a leg over her bolster. "Can't a friend just come to say hi?"_

 _"You and I," she pointed at him before looking at herself. "Are not friends. What do you want?"_

 _"Fine, fine. Serena made me drop off some science project you two were working on. She's helping mom with something so she couldn't come."_

 _"Oh. Well, did you drop it off?" She asked pointedly._

 _"Yup."_

 _"Great." She marched over to him before grabbing his arm and attempting to drag him out._

 _"Cool it Waldorf!" he barked as he secured his arm and smoothed down his suit. "It's a limited edition Versace. Uncle Gianni made it personally for me."_

 _"I don't care. Both Gianni AND Donatella visit me regularly, you're not special," she rubbed the back of her neck. "You know what, it doesn't matter. Leave Chuck."_

 _He shot her an agitated look. "I'm Chuck Bass," he announced._

 _"And I'm Blair Waldorf," she said lamely. "Just because you're Chuck Bass doesn't mean you're significant."_

 _"You've wounded me, Waldorf," he feigned a heartache before throwing her a dark look and stomping towards the door. Nearly getting out, he paused. "You're not fat Blair."_

 _She turned around, but too slowly to be normal. When she opened her mouth, her voice trailed slowly, and only heavy heaves of breath could be heard in the silent room. There was sadness in her heart, a weakness that Chuck Bass, of all people, had detected. How had he heard? How did he know?_

 _"I heard what your mom said downstairs. I was in the kitchen, stealing those oatmeal cookies that Dorota makes. Don't let Eleanor get to your head, okay? You're not fat."_

 _"And don't try to hurt yourself," he added as an after-thought._

 _And then Chuck Bass disappeared and left a wonderfully warm and light feeling blooming in her heart._

* * *

 _Present day_

Blair was sure she was red. She could feel the heat growing in her cheeks, and by now, they must be beyond an attractive rosiness. They must be marking her out as a social incompetent, a reject. Her insecurities were written large across her face and had nowhere to disguise themselves. As her anxiety mounted, they became a circle, like a song stuck on repeat. The same feelings that had ran through her—excitement, nervousness, humiliation—when she had first confessed to him resurfaced and pooled in her stomach.

"Get a hold of yourself," she murmured as she watched him grab a cup from a nearby waiter. "It's been five years."

And those five years had changed him for the better. He was no longer the skinny seventeen year old with purple Hermès scarves. His tastes had refined, and he now opted for charcoal gray suits and pale blue shirts. He had even switched those atrocious patterned bow ties for solid colored ones. His usual gelled back dark hair was styled carefully and tousled every so gently that made it seem like he had just tumbled out of his bed.

And as he made his way over to her, she realized that somethings still had not changed. People moved aside for him when he walked; they wrote tragic Great Gatsby-like novels because that was who he was—intriguing, confusing and larger than life and covered in a perpetual air of mystery. And then there was her, Blair who was as transparent as clear water. People...Chuck could see down to her very core and could predict her actions before she realized, and the very thought made her shudder ever so slightly.

"Thank you," she shot him a grateful smile as she took the glass from him, careful not to remind him of her confession years ago. "You never explained the secrecy."

"You're not going to let that go?"

She shook her head. "Of course not."

"I just wanted to surprise my sister," he trailed off.

She eyed him skeptically, eyebrow raised at the simple answer. "There's more."

"You've always been curious," he spoke with a slight smirk. "Don't worry Waldorf, it's just that."

She nodded, unsure whether she should disbelieve him wholeheartedly or believe him with skepticism. They fell into a comfortable silence as Chuck leaned against a wall and she shifted her weight between her feet. The party raged with parents and teens applauding loudly as Rufus Humphrey played another popular number. Though the music thundered, she could feel her heart pounding loud enough that she was sure every person in the room could hear it.

She tried to take in every detail of the scene to distract herself, the way Serena stood stoically as Carter Baizen attempted to converse with her or the way Nate smiled a little too widely at his partner or how Dan Humphrey had abandoned his poor mentor for the security of a corner and his marble notebook.

But even though her eyes were almost tearing up because of her fixed stare at everyone and everything occurring in front of her, she could notice every change in his posture. Every few seconds he would grip his glass so tight that an otherwise hidden vein resurfaced like a bruised thumb and then he would relax his fingers before repeating the entire thing like a ritual. He tapped his foot against one of the chairs in a rhythmic pum-padump-pum-pum.

Was he noticing her too? Probably not, but she wanted to entertain the thought. She always had a rather active imagination. She was just about to ask him whether Bart knew he was here when a squeal followed by a running Serena interrupted her thoughts. The blonde scurried past Carter before launching herself into her brother's arms and holding him as if she hadn't seen him in years.

She snuggled in, "You idiot! Why didn't you tell me that you were coming today?"

Chuck snickered, "I wanted to surprise you and well, where else would I rather be? I couldn't miss your graduation. Plus, I'm got paired up with Blair."

At that moment, his arms squeezed a fraction tighter, and Serena breathed more slowly, her body melting into her brother's as every muscle lost its tension to the air. Blair didn't know what it was about her best friend, but she attracted disaster wherever she went. She had car accidents, lost her passport multiple times during impromptu trips and got involved with low-level crimes. Admittedly, she was the softest person she knew, but there was a part of her that thought she could rescue everyone - from criminals to homeless people- if she just showed them enough love.

Blair would often tell her Serena utterly naive, but the blonde would melt her with a grin that would take her back to when they were kids. There were days when she would message late at night to say that she's going to the soup kitchen to rescue some more souls and when Blair would tag along, her best friend would joke that she's "finally seen the light."

But Blair was never the "everyday hero." That job was for her brother. He made sure that she didn't hand over her bank card and PIN to some random person and even from Yale, he somehow managed to cover for his sister's white lies and petty crimes. If there was one person Chuck Bass loved more than himself, it was his little sister. Blair blinked, suddenly feeling guilty for intruding at such an intimate moment between the two siblings.

Serena finally let go, a wicked grin on her face. "B, you never told me he was coming!"

"He never told me," she protested weakly. "It's not like we talk every day." She could feel his gaze on her and when she turned ever so slightly, her eyes collided with his. It was as if the air had been sucked out of the room and then let in so quickly that it almost knocked her off his feet. His eyes were dark, bottomless, and she felt herself falling in their depth.

Before she could look away, Serena tugged her brother's arms. "Come on, mom and dad will be so excited," Serena giggled. "I just need to talk to Blair for a second."

He eyed them skeptically, and his eyes shifted until they met her's again and searched for an explanation that she couldn't provide.

"Go," Serena pushed him towards the center of the party, near the bar. "I'll be right back." He took slow, languish steps away from them.

"B, what are you doing?" Serena's voice was hushed and quiet.

"What?"

"You like him," she accused, her blue eyes widening. "Again."

"I do not," Blair defended quickly, afraid that she would meddle in and play matchmaker. "Of course not."

"Good, you shouldn't be," she warned, her eyebrows snapping into a frown. "You'll end up getting hurt." Blair wanted to laugh at her. She's been hurt multiple times before because of him...and Nate and Serena. So what if Chuck Bass was dangerous and notorious? He was someone she'll never be, and she wanted to indulge and bathe herself in her obsession. She wanted to get hurt. Again.

Serena took one last pitiful look at her. "B, he has a girlfriend."

And then Serena turned her back before she could realize how pale she had gotten. She wanted to leave, run away from here until she was secure under her blanket where her thoughts were not convoluted by the man standing a few feet away from her. Serena's words tattered, frayed and stripped her heart until it was mush.

"B?" Serena paused and looked back when she realized Blair was not behind her.

Sighing, she plastered on the biggest smile she could muster because she couldn't say anything. She didn't have anything to say because Chuck Bass had robbed her of her words and her heart.

* * *

AN: Thank you so much for reading and reviewing! A shout out to JNYC, don'tcallmeprincess, golnazbahadori497 and Guest (I wish you left your name) for your kind words! Next chapter should be up in a couple of days. The entire story will be told in a series of flashbacks and what happens in the present. I hope the flashbacks provide some background into the nature of Chuck and Blair's relationship growing up and what led to them falling for each other.

ALSO, please let me know if you like where this story is heading. I have an outline of everything, but it is a very flexible one.

Thanks,

V


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